EP0448445B1 - Composition liquide non-aqueuse à caractère ionique et son utilisation comme solvant - Google Patents

Composition liquide non-aqueuse à caractère ionique et son utilisation comme solvant Download PDF

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Publication number
EP0448445B1
EP0448445B1 EP91400674A EP91400674A EP0448445B1 EP 0448445 B1 EP0448445 B1 EP 0448445B1 EP 91400674 A EP91400674 A EP 91400674A EP 91400674 A EP91400674 A EP 91400674A EP 0448445 B1 EP0448445 B1 EP 0448445B1
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Prior art keywords
nickel
composition
composition according
complex
liquid
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Expired - Lifetime
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EP91400674A
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German (de)
English (en)
French (fr)
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EP0448445A2 (fr
EP0448445A3 (en
Inventor
Yves Chauvin
Dominique Commereuc
Isabelle Guibard
André Hirschauer
Hélène Olivier
Lucien Saussine
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IFP Energies nouvelles
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IFP Energies nouvelles
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
    • B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
    • B01J31/0281—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member
    • B01J31/0284—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member of an aromatic ring, e.g. pyridinium
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
    • B01J31/0287—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing atoms other than nitrogen as cationic centre
    • B01J31/0288—Phosphorus
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/06—Aluminium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/06—Aluminium compounds
    • C07F5/061—Aluminium compounds with C-aluminium linkage
    • C07F5/064—Aluminium compounds with C-aluminium linkage compounds with an Al-Halogen linkage
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/20—Olefin oligomerisation or telomerisation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/84—Metals of the iron group
    • B01J2531/847—Nickel
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0235—Nitrogen containing compounds
    • B01J31/0239—Quaternary ammonium compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0255—Phosphorus containing compounds
    • B01J31/0267—Phosphines or phosphonium compounds, i.e. phosphorus bonded to at least one carbon atom, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, the other atoms bonded to phosphorus being either carbon or hydrogen
    • B01J31/0268—Phosphonium compounds, i.e. phosphine with an additional hydrogen or carbon atom bonded to phosphorous so as to result in a formal positive charge on phosphorous
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/22—Organic complexes
    • B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
    • B01J31/2208—Oxygen, e.g. acetylacetonates
    • B01J31/2226—Anionic ligands, i.e. the overall ligand carries at least one formal negative charge
    • B01J31/223—At least two oxygen atoms present in one at least bidentate or bridging ligand
    • B01J31/2234—Beta-dicarbonyl ligands, e.g. acetylacetonates

Definitions

  • the present invention relates to a non-liquid composition aqueous ionic in nature resulting from the contacting of at least an aluminum alkyl dihalide with at least one ammonium halide quaternary or / and at least one quaternary phosphonium halide, said composition being liquid below approximately 80 ° C. and, from preferably at temperatures less than or equal to about 40 ° C.
  • the present invention also relates to the use of said liquid composition as solvent (in particular of catalysts).
  • nonaqueous ionic compositions liquids below room temperature and one of which constituents is soluble in aliphatic hydrocarbons. Most studied are formed by the mixture of trichloride or tribromide aluminum with chlorides or bromides of N-alkylpyridinium and N, N ′ - dialkyl imidazolium. These liquid ionic compositions are called "molten salts" (C.H. HUSSEY, Advances in Molten Salts Chemistry, vol. 5, p. 185, Elsevier, New-York, 1983).
  • At least one dihalide e.g. a dichloride or a dibromide
  • at least one halide for example a quaternary ammonium chloride or bromide
  • at least one phosphonium halide e.g. chloride or bromide
  • at least one trihalide aluminum for example a trichloride or an aluminum tribomide
  • liquid composition is stable over time.
  • the patent FR-1,461,819 describes a mixture of compound M e X m R n with a quaternary onium salt ⁇ N (ouP) R 1 R 2 R 3 R 4 X, M e representing Al; X halogen; R C1-C6 alkyl; R1, R2, R3 or R4 being a hydrocarbon residue, met n being equal to 0, 1, 2 or 3.
  • the mixture obtained is used as an electrolyte.
  • a dimerization process operates in the homogeneous phase, in the presence of AlRX 2 , X being a halogen and R a hydrocarbon residue, and with a catalyst.
  • the catalyst results from the mixture of a transition metal compound with a complex of formula RPX 4 - AlX 3 in which RPX 4 is a tetrachlorophosphite derived from tetrachloro-orthophosphoorous acid, that is to say a derivative anionic.
  • An object of the present invention is a composition containing a catalyst and a solvent for said catalyst, wherein said solvent is a non-liquid composition aqueous ionic in nature resulting from the contacting of at least one dihalide of aluminum alkyl with at least one quaternary ammonium halide or / and minus a quaternary phosphonium halide, said composition being liquid below from about -80 ° C, composition in which said ammonium halide quaternary and said quaternary phosphonium halide respectively respond to general formulas NR1R2R3R4X and PR1R2R2R4X, where X represents a halogen chosen from bromine chlorine, R1, R2, R3 and R4, identical or different, each represent an alkyl group comprising 1 to 12 carbon atoms or R1 and R2 together form an alkylene residue of 4 to 10 carbon atoms, R3 and R4, identical or different, each represents an alkyl group comprising 1 to 12 carbon atoms
  • alkyl aluminum dihalides which can be used in the context of the invention preferably correspond to the general formula Al 2 X 4 R 2 where each X represents a halogen, chosen for example from chlorine and bromine, each R represents a hydrocarbyl residue comprising 1 to 12 carbon atoms, aromatic or aliphatic, branched or linear chain.
  • dichloromethylaluminium (common name of tetrachlorodimethyldialuminium of formula Al 2 Cl 4 (CH 3 ) 2 ), dibromomethylaluminium (Al 2 Br 4 (CH 3 ) 2 ), dichloroethylaluminim, dibromoethylaluminium, dichloro n-hexylaluminium, dichloroisobutylaluminium.
  • dichloromethylaluminium common name of tetrachlorodimethyldialuminium of formula Al 2 Cl 4 (CH 3 ) 2
  • dibromomethylaluminium Al 2 Br 4 (CH 3 ) 2
  • dichloroethylaluminim dibromoethylaluminium
  • dichloro n-hexylaluminium dichloroisobutylaluminium
  • quaternary ammonium halides and the quaternary phosphonium halides which can be used in the context of the invention preferably correspond to the respective general formulas NR 1 R 2 R 3 R 4 X, and PR 1 R 2 R 3 R 4 X, or X represents a halogen, chosen for example from chlorine and bromine, R 1, R 2 , R 3 and R 4 , identical or different, each representing an aliphatic (saturated or unsaturated) or aromatic alkyl group, comprising 1 to 12 atoms of carbon.
  • R 1, R 2 , R 3 and R 4 can also form a ring with the nitrogen or phosphorus atom; thus R 1 and R 2 can together form an alkylene residue of 4 to 10 carbon atoms, R 3 and R 4 being defined as above.
  • the ammonium halides and the phosphonium halides can be formed from at least one nitrogen or phosphorus heterocycle comprising 1, 2 or 3 nitrogen or phosphorus atoms.
  • ammonium or phosphonium halides there may be mentioned tetrabutylphosphonium chloride, tetrabutylphosphonium bromide, N-butylpyridinium chloride, ethylpyridinium bromide, 3-methylbutyl chloride imidazolium, 1-methyl-3-ethyl chloride imidazolium.
  • tetrabutylphosphonium chloride tetrabutylphosphonium bromide
  • N-butylpyridinium chloride ethylpyridinium bromide
  • 3-methylbutyl chloride imidazolium 1-methyl-3-ethyl chloride imidazolium.
  • the compounds entering into the composition according to the invention can be mixed in any order.
  • Mixing can be done by simple contacting of said compounds followed by stirring, until a homogeneous liquid phase is obtained (i.e. the liquid composition according to the invention).
  • Mixing can also be done advantageously in the presence of a saturated aliphatic hydrocarbon solvent which dissolves, for example, alkyl aluminum dihalide (s); in this case, after obtaining two clear liquid phases, the phase supernatant consisting essentially of the hydrocarbon solvent is eliminated in order to leave only the liquid composition according to the invention.
  • a saturated aliphatic hydrocarbon solvent which dissolves, for example, alkyl aluminum dihalide (s); in this case, after obtaining two clear liquid phases, the phase supernatant consisting essentially of the hydrocarbon solvent is eliminated in order to leave only the liquid composition according to the invention.
  • the relative proportions of the compounds entering into the composition according to the invention depend on the desired properties, both chemical and physical, for the composition according to the invention.
  • N 1 of the moles of the aluminum alkyl dihalide (s), and optionally, of the aluminum trihalide (s), counted in equivalents of aluminum atoms is equal to the number N 2 of moles of the aluminum halide (s) quaternary ammonium or / and quaternary phosphonium halide (s), counted in equivalents of halide atoms
  • the liquid composition obtained is said to be "neutral”; if N 1 is greater than N 2 , the liquid composition obtained is called “acid”; if N 1 is less than N 2 , the liquid composition obtained is said to be "basic".
  • Liquid compositions (or "molten salts") according to the present invention can be used as solvents (catalysts especially).
  • the neutral complexes can then be transformed into complexes of an anionic nature in the basic "molten salts” and cationic in the acidic "molten salts”; thus, the nickel acetylacetonate introduced into the basic liquid "molten salt” consisting of 1 mole of 1-methyl-3-butyl imidazolium chloride and 0.9 mole of dichloroethylaluminum is quantitatively transformed into a [NiCl 4 ] 2- complex.
  • Liquid compositions can also serve as catalyst solvents, for example example of catalysts based on transition metal complexes, in particular of dimerization, co-dimerization or oligomerization such than nickel complexes.
  • catalysts based on transition metal complexes in particular of dimerization, co-dimerization or oligomerization such than nickel complexes.
  • the use of complexes is no longer limited, as in French patent 2611700, to complexes already comprising at least one transition metal-carbon bond or transition metal-hydrogen or to complexes with a low degree of oxidation, but to most of the complexes.
  • the catalysts which can be used, in a liquid composition (or "molten salt") according to the invention, for the dimerization, the co-dimerization or the oligomerization of olefins are any complexes of nickel, apart from the complexes of nickel solvated by active proton compounds such as water, alcohols, organic acids, ammonia.
  • nickel acetylacetonate complexes of halides or nickel sulphate such as (NiCl 2 , 2 pyridine), (NiCl 2 , 2PiPr 3 ), (NiBr 2 , 2PBu 3 ), (NiSO 4 , 2PBu 3 ), nickel octoate, nickel alcoholates.
  • Nickel compounds described in French patent 2611700 which comprise at least one nickel-carbon or nickel-hydrogen bond, or which are at a valence of less than 2; by way of examples of such compounds, mention may be made of biscyclooctadiene nickel, methallylnickel chloride, bisallylnickel, allylnickel chloride, allylnickel bromide.
  • the amount of nickel complex (s) contained in the "molten salt” according to the invention, for the dimerization, the co-dimerization or the oligomerization of olefins, is generally between 0.01 mole. 1 -1 and 2 moles. 1 -1 , preferably between 0.1 and 100 moles. 1 -1 ; the optimum proportion depends on the nature of the nickel complex and on the composition of the "molten salt” according to the invention. Preferably, we will place freely in the "acid” domain of the "molten salt” and we will adjust the amount of complex to the excess of the molar fraction of aluminum aluminum dihalide (s) contained in the "molten salt". ".
  • the olefins likely to be dimerized, co-dimerized or oligomerized by the catalyst (s) contained in a "molten salt” according to the invention are the same as those which are dimerized by the nickel-based catalysts used in a hydrocarbon or halohydrocarbon medium, for example ethylene, propylene, butenes -1 and -2, styrene.
  • the olefin is brought into contact with the "molten salt" phase containing the nickel complex (s) and preferably a efficient phase transfer by vigorous agitation.
  • the phases are separated by any suitable means; for example we let the mixture settle and the upper phase is drawn off dimers, co-dimers and / or oligomers.
  • the temperature at which the reaction of dimerization, co-dimerization or oligomerization, can also be low as permitted by the composition of "molten salt” and the activity of catalyst, for example from -50 ° C to +80 ° C.
  • the pressure is generally maintained between 0.01 and 10 Mpa, the high pressures being used in particular for ethylene.
  • the lower homogeneous liquid phase consists of a liquid composition at room temperature with a titer of 0.43 N.

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EP91400674A 1990-03-20 1991-03-12 Composition liquide non-aqueuse à caractère ionique et son utilisation comme solvant Expired - Lifetime EP0448445B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR9003651A FR2659871B1 (fr) 1990-03-20 1990-03-20 Composition liquide non aqueuse a caractere ionique et son utilisation comme solvant. invention de mm. yves chauvin, dominique commereuc, isabelle guibard, andre hirschauer, helene olivier, lucien saussine.
FR9003651 1990-03-20

Publications (3)

Publication Number Publication Date
EP0448445A2 EP0448445A2 (fr) 1991-09-25
EP0448445A3 EP0448445A3 (en) 1992-01-15
EP0448445B1 true EP0448445B1 (fr) 1999-01-13

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US (1) US5104840A (ja)
EP (1) EP0448445B1 (ja)
JP (1) JP3072352B2 (ja)
AT (1) ATE175674T1 (ja)
CA (1) CA2038712C (ja)
DE (1) DE69130746T2 (ja)
DK (1) DK0448445T3 (ja)
FR (1) FR2659871B1 (ja)
ZA (1) ZA912014B (ja)

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ZA912014B (en) 1992-11-25
CA2038712C (fr) 2003-10-07
EP0448445A2 (fr) 1991-09-25
DK0448445T3 (da) 1999-08-30
JPH04217633A (ja) 1992-08-07
FR2659871B1 (fr) 1992-06-05
ATE175674T1 (de) 1999-01-15
EP0448445A3 (en) 1992-01-15
FR2659871A1 (fr) 1991-09-27
JP3072352B2 (ja) 2000-07-31
DE69130746D1 (de) 1999-02-25
US5104840A (en) 1992-04-14
DE69130746T2 (de) 1999-07-22

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